Patent FR-2920781-A1 (FR)
Title: New cationic azo thiol/disulfide compounds useful as dye for coloring keratin fibers, preferably human keratin fibers such as hair
Inventor: DAVID HERVE
IPC: A61K8/46
Filed: 2007-09-11
Abstract: Cationic azo thiol/disulfide compounds (A) and their organic acid addition salts, mineral salts, solvates, tautomers or optical and geometrical isomers as dye are new, where the electroneutrality of (A) is assured by one or more anionic counter-ions. Cationic azo thiol/disulfide compounds (A) of formula ([W 1-N=N-W 2-NR-W 3-NR2a-L-CH 2-S] x-[Y 1] yAn ->) (I) or ([W 5-NR-W 2-N=N-W 4-L-CH 2-S] x-[Y 1] yAn ->) (II) and their organic acid addition salts, mineral salts, solvates, tautomers or optical and geometrical isomers as dye are new, where the electroneutrality of (A) is assured by one or more anionic counter-ions. W 1pyridinium radical of formula (IIb) or imidazole group of formula (IIa); W 2substituted phenyl group of formula (III); W 3substituted phenyl group of formula (IV); W 4imidazole group of formula (Va) or pyridinium radical of formula (Vb); W 5substituted phenyl group of formula (VI); R, R2a : H, 1-4C alkyl (optionally substituted) or OH; R 11-6C alkyl, aryl-1-6C-alkyl, (hetero)aryl or heteroaryl(1-6C)alkyl (all optionally substituted), cycloalkyl(1-6C)alkyl or heterocycloalkyl(1-6C)alkyl; either R 2-R 51-6C alkyl, 2-4C (poly)hydroxyalkyl, OH, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, alkoxycarbonyl (R 11O-CO-), alkoxycarbonyloxy (R 11CO-O-), amino (optionally substituted by one or more 1-4C alkyl and containing OH) (where two radical alkyl radical together with N form 5 or 6 membered heterocycle containing O or N), alkylcarbonylamino (R 11CO-NR 12-), dialkylaminocarbonyl (R 12R 12CO-NR 12-), guanidium group (R 12R 12N-C(=NH 2 +>)-NR 12) or halo; or CR 2R 2, CR 3R 3, CR 4R 4condensed aromatic 6 membered cycle (optionally substituted with OH, 1-4C alkyl, hydroxycarbonyl or alkoxy carbonyl (R 11OOC)), (alkyl)sulfonylamino (R 11SO 2NR 13) or methylcarbonylamino, where the two alkyl groups together optionally with N form 5 or 6 membered heterocycle containing heteroatoms of N; R 13H, 1-4C alkyl, 1-4C alkoxy, amino (optionally substituted by 1-4C alkyl and containing OH); R 111-4C alkyl; R 12H or 1-4C alkyl; m, n : 0-4, when m or n is less than 4, then the carbon atoms of the aromatic cycle is optionally substituted and carries H; o : 0-5, when o is less than 5, then the carbon atoms of the aromatic cycle is unsubstituted and carries H; e : 0-2, when e is less than 2, then the carbon atoms of the aromatic cycle is unsubstituted and carries H; G : O, S or -N(Alk)-; Alk : 1-4C alkyl; L : covalent bond (sigma bond), divalent group -CG-, 1-20C bivalent hydrocarbon chain (optionally substituted and optionally interrupted by one or more divalent groups or their combinations, two divalent groups or their combinations are separated by divalent hydrocarbon chain comprising -N(R)-, N +>(R)R 0-, An ->, -O-, -S-, -C(O)-, cationic heterocycle or cationic heteroaryl (Het +>An ->), cationic heterocycle comprising 5-10 chains such that piperazinyl) or (hetero)aryl (optionally substituted), where L does not comprises diazo, hydrazino, aminooxy, nitro, nitroso or peroxide; R : 1-4C alkyl, 2-6C (poly)hydroxyalkyl, alkoxy(1-6C)alkyl, aryl, aryl(1-6C)alkyl, (1-4C)alkylcarbonylamino(1-6C)alkyl or amino(1-4C)alkyl (in which the amino is substituted by one or more 1-4C alkyl, alkyl(1-6C)carbonyl or (1-4C)alkylcarbonylamino); R 0H or R; Het +>cationic heterocycle containing 5-10 chains (optionally saturated) or cationic heteroaryl containing 5-10 chains; x : 1 or 2; y : 0 or 1; Y 1H, alkali metal, alkaline earth metal, ammonium group of formula (N +>Ralpha Rbeta Rgamma Rdelta ), phosphonium group of formula (P +>Ralpha Rbeta Rgamma Rdelta ), or protecting group of functional thiol; Ralpha , Rbeta , Rgamma , Rdelta : 1-4C alkyl; and An ->anionic counter-ion, where the electroneutrality of (A) being assured by one or more An ->anions. Provided that: when x is 1 then y is 1; when x is 2 then y is 0; the bond (a) in (IIa), (IIb), (III), (IV), (Va), (Vb), or (VI) connects the groups W 1, W 2and W 4to N, in the case of formulas (IIa), (IIb), (Va), (Vb), when two R 2radical carried by two adjacent carbon atoms form an aromatic cycle such as benzyl; the bond (a) can connect W 1, W 2or W 4to N by aromatic cycle intermediate; the bond (a 1) in (III), (IV) and (VI) connects the groups W 2, W 3and W 5to -NR-; and the bond (b) in (Va) or (Vb) connects the groups W 4to the bond L; and the bond (a 2) in (IV) connects the groups W 3to -NR2a. Independent claims are included for: (1) dye composition comprising a dye compound (I) or (II) in a cosmetic medium; (2) a method of coloring of keratin fibers, comprising applying the composition comprising (A) on keratin fibers; and (3) multi-compartment device comprising: a first compartment containing a dye composition; and a second compartment containing a reducing agent. [Image] [Image].